Anilide derivatives and their use for combating botrytis

ABSTRACT

The use of nicotinic anilide derivatives of the general formula ##STR1## where the substituents have the following meanings: R 1  halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl 
     R 2  unsubstituted or halogen-substituted alkyl, unsubstituted or halogen-substituted alkenyl, alkynyl, unsubstituted or halogen-substituted alkoxy, unsubstituted or halogen-substituted alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenyloxy 
     for combating Botrytis, and nicotinic anilides of the formula I.

This is a division, of application Ser. No. 07/973,976, filed on Nov. 9, 1992, U.S. Pat. No. 5,330,995.

The present invention relates to the use of anilide derivatives of the general formula ##STR2## where A has the following meanings: pyridin-3-yl substituted in the 2-position by halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl,

phenyl substituted in 2-position by methyl, trifluoromethyl, chlorine, bromine or iodine,

2-methyl-5,6-dihydropyran-3-yl, 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl, 2-methyl-5,6-dihydro-1,4oxathiin-3-yl-4-oxide, 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl-4,4-dioxide; 2-methyl-furan-3-yl substituted in the 4- and 5-positions by hydrogen or methyl; thiazol-5-yl substituted in the 2- and 4-positions by hydrogen, methyl, chlorine or trifluoromethyl; thiazol-4-yl substituted in the 2- and 5-positions by hydrogen, methyl, chlorine or trifluoromethyl; 1-methylpyrazol-4-yl substituted in the 3- and 5-positions by methyl, chlorine or trifluoromethyl; or oxazol-5-yl substituted the 2- and 4-positions by hydrogen, methyl or chlorine, and

R has the following meanings: unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ C₆ -cycloalkenyloxy, or phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen,

for combating Botrytis.

The present invention further relates to novel anilide derivatives.

It is known to use nicotinic anilides, e.g., 2-chloronicotic-2'-ethylanilide (US 4,001,416) and 2-chloronicotic-3'-isopropyl-anilide (DE 26 11 601), as fungicides.

We have now found that the anilide derivatives defined at the outset have a good action on Botrytis.

In view of their action, those compounds are preferred in which the substituents have the following meanings:

halogen, e.g., fluorine, chlorine and bromine,

alkyl, especially ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl or dodecyl, where alkyl may bear from one to three of the above-mentioned halogen atoms, especially fluorine and chlorine, alkenyl, such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2 -hexenyl, 3hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,

4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, especially 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl, where alkenyl may bear from one to three of the abovementioned halogen atoms, especially fluorine and chlorine,

alkynyl, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,2-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl,

alkoxy, especially ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,2-dimethylpropoxy, 1,1-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1-ethyl-2-methylpropoxy, n-heptyloxy, 1-methylhexyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 4-methylhexyloxy, 5-methylhexyloxy, 1-ethylpentyloxy, 2-ethylpentyloxy, 1-propylbutoxy, octyloxy, decyloxy, and dodecyloxy, where alkoxy may bear from one to three of the above-mentioned halogen atoms, especially fluorine and chlorine,

alkenyloxy such as 2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl2-propenyloxy, 1-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy, especially 2-propenyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy and 3-methyl-2-pentenyloxy;

where alkenyloxy may bear from one to three of the above-mentioned halogen atoms, especially fluorine and chlorine;

alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-methyl-2-butynyloxy, 1,1-dimethyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-alkynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy, 1-methyl-4-pentynyloxy, 2-methyl-3-pentynyloxy, 2-methyl-4-pentynyloxy, 3-methyl-4-pentynyloxy, 4-methyl-3-pentynyloxy, 1,1-dimethyl-2-butynyloxy, 1,1-dimethyl-3-butynyloxy, 1,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3-butynyloxy, 1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, 2-ethyl-3-butynyloxy and 1-ethyl-1-methyl-2-propynyloxy, preferably 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and 1-methyl-2-butynyloxy,

C₃ -C₆ -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclotpentyl and cyclohexyl, where cycloalkyl is unsubstituted or substituted by one to three C₁ -C₄ -alkyl radicals;

C₄ -C₆ -cycloalkenyl, such as cyclobutenyl, cyclopentenyl and cyclohexenyl, which is unsubstituted or substituted by one to three C₁ -C₄ -alkyl radicals;

C₅ -C₆ -cycloalkoxy such as cyclopentyloxy or cyclohexyloxy, which may be substituted by one to three C₁ -C₄ -alkyl radicals;

C₅ -C₆ -cycloalkenyloxy such as cyclopentyloxy or cyclohexaryloxy, which may be substituted by one to three C₁ -C₄ -alkyl radicals.

For combating Botrytis, the use of nicotinic anilide derivatives of the formula I in which the substituents have the meanings given below is preferred: ##STR3## R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl

R² unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆ -cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆ -cycloalkenyloxy.

The compounds of the formula I are obtained for instance by reacting a correspondingly substituted nicotinic halide of the formula 2 ##STR4##

Hal denoting chlorine or bromine, with an ortho-substituted aniline of the formula 3 in the presence of a base. The nicotinic acids and their halides of the formula 2 are known. The anilines of the formula 3 are known or can be prepared by known methods (Helv. Chim. Acta 60, 978 (1977); Zh. Org. Khim 26, 1527(1990); Heterocyclus 26, 1885 (1987); Izv. Akad. Nauk. SSSR Ser. Khim 1982, 2160).

Compounds of the formula I in which R¹ is chlorine and R² has the meanings given above are particularly preferred.

                                      TABLE 1                                      __________________________________________________________________________     Compounds of the formula I                                                      ##STR5##                            I                                                                  Phys. data                                            No. R1    R2             m.p. [°C.]                                     __________________________________________________________________________     1.1 F     n-C.sub.3 H.sub.7                                                    1.2 F     i-C.sub.3 H.sub.7                                                    1.3 F     sec.-C.sub.4 H.sub.9                                                                          52-54                                                 1.4 F     i-C.sub.4 H.sub.9                                                                             87-89                                                 1.5 Cl    n-C.sub.3 H.sub.7                                                                             103-104                                               1.6 Cl    n-C.sub.4 H.sub.9                                                    1.7 Cl    sec.-C.sub.4 H.sub.9                                                                          94-96                                                 1.8 Cl    i-C.sub.4 H.sub.9                                                                             99-101                                                1.9 Cl    tert.-C.sub.4 H.sub.9                                                                         118-120                                               1.10                                                                               Cl    n-C.sub.5 H.sub.11                                                   1.11                                                                               Cl    sec.-C.sub.5 H.sub.11                                                1.12                                                                               Cl    n-C.sub.6 H.sub.13                                                   1.13                                                                               Cl    n-C.sub.7 H.sub.15                                                   1.14                                                                               Cl    sec.-C.sub.7 H.sub.15                                                1.15                                                                               Cl    n-C.sub.8 H.sub.17                                                   1.16                                                                               Cl    n-C.sub.10 H.sub.23                                                  1.17                                                                               Cl    n-C.sub.12 H.sub.25                                                  1.18                                                                               Cl    1-Methylvinyl  90-91                                                 1.19                                                                               Cl    2-Methylvinyl                                                        1.20                                                                               Cl    Allyl                                                                1.21                                                                               Cl    2-Methylallyl                                                        1.22                                                                               Cl    2-Ethylallyl                                                         1.23                                                                               Cl    1-Methylallyl                                                        1.24                                                                               Cl    1-Ethylallyl                                                         1.25                                                                               Cl    1-Methyl-2-butenyl                                                   1.26                                                                               Cl    1-Ethyl-2-butenyl                                                    1.27                                                                               Cl    1-Isopropyl-2-butenyl                                                1.28                                                                               Cl    1-n-Butyl-2-butenyl                                                  1.29                                                                               Cl    1-Methyl-2-pentenyl                                                  1.30                                                                               Cl    1,4-Dimethyl-2-pentenyl                                              1.31                                                                               Cl    Propargyl                                                            1.32                                                                               Cl    2-Butynyl                                                            1.33                                                                               Cl    3-Butynyl                                                            1.34                                                                               Cl    Ethoxy         131-132                                               1.35                                                                               Cl    Propoxy                                                              1.36                                                                               Cl    1-Methylethoxy 65-67                                                 1.37                                                                               Cl    n-Butoxy       84-85                                                 1.38                                                                               Cl    1-Methylpropoxy                                                                               72-74                                                 1.39                                                                               Cl    2-Methylpropoxy                                                                               81-84                                                 1.40                                                                               Cl    1,1-Dimethylethoxy                                                   1.41                                                                               Cl    n-Pentyloxy                                                          1.42                                                                               Cl    n-Hexyloxy                                                           1.43                                                                               Cl    n-Hepyloxy                                                           1.44                                                                               Cl    n-Octyloxy                                                           1.45                                                                               Cl    2-Ethylhexyloxy                                                      1.46                                                                               Cl    n-Decyloxy                                                           1.47                                                                               Cl    2-Propenyloxy  86-88                                                 1.48                                                                               Cl    2-Butentyloxy  92-95                                                 1.49                                                                               Cl    2-Methyl-2-propenyloxy                                                                        75-76                                                 1.50                                                                               Cl    2-Pentenyloxy                                                        1.51                                                                               Cl    3-Pentenyloxy                                                        1.52                                                                               Cl    3-chloro-2-propenyloxy                                               1.53                                                                               Cl    2,3-Dichloro-2-propenyloxy                                           1.54                                                                               Cl    2,3,3-Trichloro-propenyloxy                                          1.55                                                                               Cl    2-Propynyloxy  79-84                                                 1.56                                                                               Cl    2-Butynyl-oxy                                                        1.57                                                                               Cl    3-Butynyl-oxy                                                        1.58                                                                               Cl    1-Methyl-2-propynyloxy                                               1.59                                                                               Cl    Cyclopropyl    144-145                                               1.60                                                                               Cl    Cyclobutyl                                                           1.61                                                                               Cl    Cyclopentyl    112-114                                               1.62                                                                               Cl    Cyclohexyl     141-142                                               1.63                                                                               Cl    2-Cyclopentenyl                                                                               123-124                                               1.64                                                                               Cl    1-Cyclopentenyl                                                      1.65                                                                               Cl    2-Cyclohexenyl 92-93                                                 1.66                                                                               Cl    1-Cyclohexenyl                                                       1.67                                                                               Cl    Cyclopentyloxy 80-82                                                 1.68                                                                               Cl    Cyclohexyloxy                                                        1.69                                                                               Cl    2-Cyclopentenyloxy                                                   1.70                                                                               Cl    2-Cyclohexenyloxy                                                                             oil                                                   1.71                                                                               Br    sec.-Butyl                                                           1.72                                                                               Br    i-Butyl                                                              1.73                                                                               CH.sub.3                                                                             sec.-Butyl                                                           1.74                                                                               CH.sub.3                                                                             i-Butyl                                                              1.75                                                                               CF.sub.3                                                                             i-Propyl                                                             1.76                                                                               CF.sub.3                                                                             sec.-Butyl                                                           1.77                                                                               CF.sub.3                                                                             i-Butyl                                                              1.78                                                                               OCH.sub.3                                                                            i-Propyl                                                             1.79                                                                               OCH.sub.3                                                                            sec.-Butyl     oil NMR 0.8t(3H); 1.2d                                                         (3H); 1.6m(2H); 3.0q(1H);                                                      4.1s(3H); 7.2m(3H); 7.3m                                                       (1H); 8.3m(1H); 8.4m(1H),                                                      9.8s(1H)                                              1.80                                                                               OCH.sub.3                                                                            i-Butyl        oil NMR 0.8d(6H); 1.9m                                                         (1H); 2.5d(2H), 4.05s(3H),                                                     7.2m(4H); 7.5d(1H); 8.3d                                                       (1H); 8.4m(1H); 9.8s(1H)                              1.81                                                                               SCH.sub.3                                                                            i-Propyl                                                             1.82                                                                               SCH.sub.3                                                                            sec.-Butyl     89-91                                                 1.83                                                                               SCH.sub.3                                                                            i-Butyl        140-141                                               1.84                                                                               SO.sub.2 CH.sub.3                                                                    sec.-Butyl     191-192                                               1.85                                                                               SO.sub.2 CH.sub.3                                                                    i-Butyl        150-153                                               1.86                                                                               Cl    2-Ethylpropoxy 65-66                                                 1.87                                                                               Cl    3-Methyl-3-butenyloxy                                                                         83-84                                                 __________________________________________________________________________

MANUFACTURING EXAMPLES Example 1

At 0° C., 3.5 g of 2-chloroonicotic chloride is dripped into a solution of 2.7 g of 2-n-propylaniline and 2.0 g of triethylamine in 30 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. After dilution with 300 ml of water, there is isolated 3.2 g of 2-chloronicotic acid-2-n-propylanilide; m.p.: 103°-104° C. (No. 1.5).

Example 2

4.4 g of 2-chloroonicotic acid-2-sec.-butylanilide (Table 1, No. 7) is refluxed for 2 hours in a solution of 5.5 g of 30% strength sodium methylate solution in 20 ml of methanol. After dilution with 250 ml of water the mixture is extracted twice, each time with 100 ml of ethyl acetate. From the combined organic phases there is isolated, after drying and evaporation of the solvent, 3.8 g of 2-methoxy-nicotinic acid-2-sec.-butylanilide as an oil (No. 1.79).

Example 3

Similarly to Example 1, there is obtained from 5.7 g of 2-methylthionicotic chloroide, 4.6 g of 2-sec-butylaniline and 3.1 g of triethylamine 6.6 g of 2-methylthionicotic acid-2-sec.-butylanilide; m.p.: 89°-91° C. (No. 1.82).

Example 4

While stirring at 35° C., 2.20 g of 30% strength hydrogen peroxyde is dripped into a mixture of 2.00 g of the abovementioned product (Example 3) in 5 ml of glacial acetic acid and 0.13 g of sodium tungstate, and the mixture is stirred for 3 hours at 35° C. After dilution with 15 ml of water, removal of the crystals by suction filtration, washing with water and drying, there is obtained 1.7 g of 2-methylsulfonylnicotic acid-2-sec.-butylanilide; m.p.: 191°-192° C. (No. 1.84).

The invention further relates to the use of anilide derivatives of the formula II ##STR6## where the substituents have the following meanings: ##STR7## X methylene or sulfur R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

The compounds of the formula 2 are obtained for instance by reacting a correspondingly substituted carboxylic halide of the formula 4 with an ortho-substituted aniline of the formula 3 in the presence of a base: ##STR8##

Hal is chlorine or bromine.

The carboxylic acids and their halides ACO₂ H and A-CO-Hal (4) are known.

                  TABLE 2                                                          ______________________________________                                         Compounds of the formula II                                                     ##STR9##                                                                                                          Phys. data                                 No.   A     R                  X    mp [°C.]                            ______________________________________                                         2.1   A.sub.1                                                                              i-C.sub.3 H.sub.7  --   108-109                                    2.2   A.sub.1                                                                              n-C.sub.3 H.sub.7  --   112-114                                    2.3   A.sub.1                                                                              n-C.sub.4 H.sub.9  --                                              2.4   A.sub.1                                                                              sec.-C.sub.4 H.sub.9                                                                              --   89-90                                      2.5   A.sub.1                                                                              i-C.sub.4 H.sub.9  --   118-11                                     2.6   A.sub.1                                                                              tert.-C.sub.4 H.sub.9                                                                             --                                              2.7   A.sub.1                                                                              n-C.sub.5 H.sub.11 --                                              2.8   A.sub.1                                                                              sec.-C.sub.5 H.sub.11                                                                             --                                              2.9   A.sub.1                                                                              n-C.sub.6 H.sub.13 --                                              2.10  A.sub.1                                                                              n-C.sub.7 H.sub.15 --                                              2.11  A.sub.1                                                                              sec.-C.sub.7 H.sub.15                                                                             --                                              2.12  A.sub.1                                                                              1-Methylvinyl      --                                              2.13  A.sub.1                                                                              2-Methylvinyl      --                                              2.14  A.sub.1                                                                              Allyl              --                                              2.15  A.sub.1                                                                              2-Methylallyl      --                                              2.16  A.sub.1                                                                              2-Ethylallyl       --                                              2.17  A.sub.1                                                                              1-Methylallyl      --                                              2.18  A.sub.1                                                                              1-Ethylallyl       --                                              2.19  A.sub.1                                                                              1-Methyl-2-butenyl --                                              2.20  A.sub.1                                                                              1-Ethyl-2-butenyl  --                                              2.21  A.sub.1                                                                              1-Isopropyl-2-butenyl                                                                             --                                              2.22  A.sub.1                                                                              1-n-Butyl-2-butenyl                                                                               --                                              2.23  A.sub.1                                                                              1-Methyl-2-pentenyl                                                                               --                                              2.24  A.sub.1                                                                              1,4-Dimethyl-2-pentenyl                                                                           --                                              2.25  A.sub.1                                                                              Propargyl          --                                              2.26  A.sub.1                                                                              2-Butynyl          --                                              2.27  A.sub.1                                                                              3-Butynyl          --                                              2.28  A.sub.1                                                                              Ethoxy             --                                              2.29  A.sub.1                                                                              Propoxy            --                                              2.30  A.sub.1                                                                              1-Methylethoxy     --                                              2.31  A.sub.1                                                                              n-Butoxy           --                                              2.32  A.sub.1                                                                              1-Methylpropoxy    --   46-84                                      2.33  A.sub.1                                                                              2-Methylpropoxy    --                                              2.34  A.sub.1                                                                              1,1-Dimethylethoxy --                                              2.35  A.sub.1                                                                              n-Pentyloxy        --                                              2.36  A.sub.1                                                                              n-Hexyloxy         --                                              2.37  A.sub.1                                                                              2-Ethylhexyloxy    --                                              2.38  A.sub.1                                                                              2-Propenyloxy      --                                              2.39  A.sub.1                                                                              2-Butentyloxy      --   62-66                                      2.40  A.sub.1                                                                              2-Methyl-2-propenyloxy                                                                            --   oil                                        2.41  A.sub.1                                                                              2-Pentenyloxy      --                                              2.42  A.sub.1                                                                              3-Pentenyloxy      --                                              2.43  A.sub.1                                                                              3-Chloro-2-propenyloxy                                                                            --                                              2.44  A.sub.1                                                                              2,3-Dichloro-2-propenyloxy                                                                        --                                              2.45  A.sub.1                                                                              2,3,3-Trichloro-propenyloxy                                                                       --                                              2.46  A.sub.1                                                                              2-Propynyloxy      --                                              2.47  A.sub.1                                                                              2-Butynyl-oxy      --                                              2.48  A.sub.1                                                                              3-Butynyl-oxy      --                                              2.49  A.sub.1                                                                              1-Methyl-2-propynyloxy                                                                            --                                              2.50  A.sub.1                                                                              Cyclopropyl        --                                              2.51  A.sub.1                                                                              Cyclobutyl         --                                              2.52  A.sub.1                                                                              Cyclopentyl        --   112-113                                    2.53  A.sub.1                                                                              Cyclohexyl         --   120-121                                    2.54  A.sub.1                                                                              2-Cyclopentenyl    --   128-129                                    2.55  A.sub.1                                                                              1-Cyclopentenyl    --                                              2.56  A.sub.1                                                                              2-Cyclohexenyl     --   95-96                                      2.57  A.sub.1                                                                              1-Cyclohexenyl     --                                              2.58  A.sub.1                                                                              Cyclopentyloxy     --                                              2.59  A.sub.1                                                                              Cyclohexyloxy      --                                              2.60  A.sub.1                                                                              2-Cyclopentenyloxy --                                              2.61  A.sub.1                                                                              2-Cyclohexenyloxy  --   oil                                        2.62  A.sub.2                                                                              i-C.sub.3 H.sub.7  CH.sub.2                                                                            99-101                                     2.63  A.sub.2                                                                              n-C.sub.3 H.sub.7  CH.sub.2                                        2.64  A.sub.2                                                                              n-C.sub.4 H.sub.9  CH.sub.2                                        2.65  A.sub.2                                                                              sec.-C.sub.4 H.sub.9                                                                              CH.sub.2                                                                            81-82                                      2.66  A.sub.2                                                                              i-C.sub.4 H.sub.9  CH.sub.2                                                                            81-83                                      2.67  A.sub.2                                                                              tert.-C.sub.4 H.sub.9                                                                             CH.sub.2                                        2.68  A.sub.2                                                                              n-C.sub.5 H.sub.11 CH.sub.2                                        2.69  A.sub.2                                                                              sec.-C.sub.5 H.sub.11                                                                             CH.sub.2                                        2.70  A.sub.2                                                                              n-C.sub.6 H.sub.13 CH.sub.2                                        2.71  A.sub.2                                                                              n-C.sub.7 H.sub.15 CH.sub.2                                        2.72  A.sub.2                                                                              sec.-C.sub.7 H.sub.15                                                                             CH.sub.2                                        2.73  A.sub.2                                                                              1-Methylvinyl      CH.sub.2                                        2.74  A.sub.2                                                                              2-Methyivinyl      CH.sub.2                                        2.75  A.sub.2                                                                              Allyl              CH.sub.2                                        2.76  A.sub.2                                                                              2-Methylallyl      CH.sub.2                                        2.77  A.sub.2                                                                              2-Ethylallyl       CH.sub.2                                        2.78  A.sub.2                                                                              1-Methylallyl      CH.sub.2                                        2.79  A.sub.2                                                                              1-Ethylallyl       CH.sub.2                                        2.80  A.sub.2                                                                              1-Methyl-2-butenyl CH.sub.2                                        2.81  A.sub.2                                                                              1-Ethyl-2-butenyl  CH.sub.2                                        2.82  A.sub.2                                                                              1-Isopropyl-2-butenyl                                                                             CH.sub.2                                        2.83  A.sub.2                                                                              1-n-Butyl-2-butenyl                                                                               CH.sub.2                                        2.84  A.sub.2                                                                              1-Methyl-2-pentenyl                                                                               CH.sub.2                                        2.85  A.sub.2                                                                              1,4-Dimethyl-2-pentenyl                                                                           CH.sub.2                                        2.86  A.sub.2                                                                              Propargyl          CH.sub.2                                        2.87  A.sub.2                                                                              2-Butynyl          CH.sub.2                                        2.88  A.sub.2                                                                              3-Butynyl          CH.sub.2                                        2.89  A.sub.2                                                                              Ethoxy             CH.sub.2                                        2.90  A.sub.2                                                                              Propoxy            CH.sub.2                                        2.91  A.sub.2                                                                              1-Methylethoxy     CH.sub.2                                        2.92  A.sub.2                                                                              n-Butoxy           CH.sub.2                                        2.93  A.sub.2                                                                              1-Methylpropoxy    CH.sub.2                                        2.94  A.sub.2                                                                              2-Methylpropoxy    CH.sub.2                                        2.95  A.sub.2                                                                              1,1-Dimethylethoxy CH.sub.2                                        2.96  A.sub.2                                                                              n-Pentyloxy        CH.sub.2                                        2.97  A.sub.2                                                                              n-Hexyloxy         CH.sub.2                                        2.98  A.sub.2                                                                              2-Ethylhexyloxy    CH.sub.2                                        2.99  A.sub.2                                                                              2-Propenyloxy      CH.sub.2                                        2.100 A.sub.2                                                                              2-Butentyloxy      CH.sub.2                                        2.101 A.sub.2                                                                              1-Methyl-2-propenyloxy                                                                            CH.sub.2                                                                            67-69                                      2.102 A.sub.2                                                                              2-Pentenyloxy      CH.sub.2                                        2.103 A.sub.2                                                                              3-Pentenyloxy      CH.sub.2                                        2.104 A.sub.2                                                                              3-chloro-2-propenyloxy                                                                            CH.sub.2                                        2.105 A.sub.2                                                                              2,3-Dichloro-2-propenyloxy                                                                        CH.sub.2                                        2.106 A.sub.2                                                                              2,3,3-Trichloro-propenyloxy                                                                       CH.sub.2                                        2.107 A.sub.2                                                                              2-Propynyloxy      CH.sub.2                                        2.108 A.sub.2                                                                              2-Butynyl-oxy      CH.sub.2                                        2.109 A.sub.2                                                                              3-Butynyl-oxy      CH.sub.2                                        2.110 A.sub.2                                                                              1-Methyl-2-propynyloxy                                                                            CH.sub.2                                        2.111 A.sub.2                                                                              Cyclopropyl        CH.sub.2                                        2.112 A.sub.2                                                                              Cyclobutyl         CH.sub.2                                        2.113 A.sub.2                                                                              Cyclopentyl        CH.sub.2                                                                            109-111                                    2.114 A.sub.2                                                                              Cyclohexyl         CH.sub.2                                                                            118-123                                    2.115 A.sub.2                                                                              2-Cyclopentenyl    CH.sub.2                                                                            87-89                                      2.116 A.sub.2                                                                              1-Cyclopentenyl    CH.sub.2                                        2.117 A.sub.2                                                                              2-Cyclohexenyl     CH.sub.2                                                                            85-87                                      2.118 A.sub.2                                                                              1-Cyclohexenyl     CH.sub.2                                        2.119 A.sub.2                                                                              Cyclopentyloxy     CH.sub.2                                                                            60-91                                      2.120 A.sub.2                                                                              Cyclohexyloxy      CH.sub.2                                        2.121 A.sub.2                                                                              2-Cyclopentenyloxy CH.sub.2                                        2.122 A.sub.2                                                                              2-Cyclohexenyloxy  CH.sub.2                                                                            oil                                        2.123 A.sub.2                                                                              i-C.sub.3 H.sub.7  S                                               2.124 A.sub.2                                                                              n-C.sub.3 H.sub.7  S                                               2.125 A.sub.2                                                                              n-C.sub.4 H.sub.9  S                                               2.126 A.sub.2                                                                              sec.-C.sub.4 H.sub.9                                                                              S    oil                                        2.127 A.sub.2                                                                              i-C.sub.4 H.sub.9  S    oil                                        2.128 A.sub.2                                                                              tert.-C.sub.4 H.sub.9                                                                             S                                               2.129 A.sub.2                                                                              n-C.sub.5 H.sub.11 S                                               2.130 A.sub.2                                                                              sec.-C.sub.5 H.sub.11                                                                             S                                               2.131 A.sub.2                                                                              n-C.sub.6 H.sub.13 S                                               2.132 A.sub.2                                                                              n-C.sub.7 H.sub.15 S                                               2.133 A.sub.2                                                                              sec.-C.sub.7 H.sub.15                                                                             S                                               2.134 A.sub.2                                                                              1-Methylvinyl      S                                               2.135 A.sub.2                                                                              2-Methylvinyl      S                                               2.136 A.sub.2                                                                              Allyl              S                                               2.137 A.sub.2                                                                              2-Methylallyl      S                                               2.138 A.sub.2                                                                              2-Ethylallyl       S                                               2.139 A.sub.2                                                                              1-Methylallyl      S                                               2.140 A.sub.2                                                                              1-Ethylallyl       S                                               2.141 A.sub.2                                                                              1-Methyl-2-butenyl S                                               2.142 A.sub.2                                                                              1-Ethyl-2-butenyl  S                                               2.143 A.sub.2                                                                              1-Isopropyl-2-butenyl                                                                             S                                               2.144 A.sub.2                                                                              1-n-Butyl-2-butenyl                                                                               S                                               2.145 A.sub.2                                                                              1-Methyl-2-pentenyl                                                                               S                                               2.146 A.sub.2                                                                              1,4-Dimethyl-2-pentenyl                                                                           S                                               2.147 A.sub.2                                                                              Propargyl          S                                               2.148 A.sub.2                                                                              2-Butynyl          S                                               2.149 A.sub.2                                                                              3-Butynyl          S                                               2.150 A.sub.2                                                                              Ethoxy             S                                               2.151 A.sub.2                                                                              Propoxy            S                                               2.152 A.sub.2                                                                              1-Methylethoxy     S                                               2.153 A.sub.2                                                                              n-Butoxy           S                                               2.154 A.sub.2                                                                              1-Methylpropoxy    S    oil                                        2.155 A.sub.2                                                                              2-Methylpropoxy    S                                               2.156 A.sub.2                                                                              1,1-Dimethylethoxy S                                               2.157 A.sub.2                                                                              n-Pentyloxy        S                                               2.158 A.sub.2                                                                              n-Hexyloxy         S                                               2.159 A.sub.2                                                                              2-Ethylhexyloxy    S                                               2.160 A.sub.2                                                                              2-Propenyloxy      S                                               2.161 A.sub.2                                                                              2-Butentyloxy      S                                               2.162 A.sub.2                                                                              1-Methyl-2-propenyloxy                                                                            S    65-67                                      2.163 A.sub.2                                                                              2-Pentenyloxy      S                                               2.164 A.sub.2                                                                              3-Pentenyloxy      S                                               2.165 A.sub.2                                                                              3-chloro-2-propenyloxy                                                                            S                                               2.166 A.sub.2                                                                              2,3-Dichloro-2-propenyloxy                                                                        S                                               2.167 A.sub.2                                                                              2,3,3-Trichloro-propenyloxy                                                                       S                                               2.168 A.sub.2                                                                              2-Propynyloxy      S                                               2.169 A.sub.2                                                                              2-Butynyl-oxy      S                                               2.170 A.sub.2                                                                              3-Butynyl-oxy      S                                               2.171 A.sub.2                                                                              1-Methyl-2-propynyloxy                                                                            S                                               2.172 A.sub.2                                                                              Cyclopropyl        S                                               2.173 A.sub.2                                                                              Cyclobutyl         S                                               2.174 A.sub.2                                                                              Cyclopentyl        S    62-64                                      2.175 A.sub.2                                                                              Cyclohexyl         S    120-122                                    2.176 A.sub.2                                                                              2-Cyclopentenyl    S    76-78                                      2.177 A.sub.2                                                                              1-Cyclopentenyl    S                                               2.178 A.sub.2                                                                              2-Cyclohexenyl     S    70-72                                      2.179 A.sub.2                                                                              1-Cyclohexenyl     S                                               2.180 A.sub.2                                                                              Cyclopentyloxy     S    88-90                                      2.181 A.sub.2                                                                              Cyclohexyloxy      S                                               2.182 A.sub.2                                                                              2-Cyclopentenyloxy S                                               2.183 A.sub.2                                                                              2-Cyclohexenyloxy  S    oil                                        2.184 A.sub.1                                                                              1-Ethylpropoxy     --   65-66                                      2.185 A.sub.1                                                                              3-Methyl-2-butenyloxy                                                                             --   oil                                        2.186 A.sub.2                                                                              1-Ethylpropoxy     CH.sub.2                                                                            oil                                        2.187 A.sub.2                                                                              1-Ethylpropoxy     S    oil                                        ______________________________________                                    

Manufacturing examples

Example 5

At 0° C., 3.1 g of 2-methylbenzoic chloride is dripped into a solution of 3.0 g of sec-butyl-aniline and 2.0 g of triethylamine in 30 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. After dilution with 500 ml of water, extraction with ethyl acetate and evaporation of the solvent, there is isolated 2-methylbenzoic acid-2-sec-butylanilide; m.p. 89°-90° C. (Compound No. 2.4).

Example 6

At 0° C., 2.5 g thionyl chloride is dripped into a solution of 3.0 g of 2-methyl-5,6-dihydropyran-3-carboxylic acid. After the mixture has been stirred for 1 hour, 2.8 g of 2-isopropylaniline is added and the whole is stirred for 12 hours at room temperature (20° C.). The pyridine is evaporated off, 50 ml of water is stirred in, the pH is adjusted to 3 with dilute hydrochloric acid, and extraction is carried out with ethyl acetate. The solvent is evaporated, the residue is mixed with diisopropyl ether, and there is isolated 3.3 g of 2-methyl-5,6-dihydropyran-3-carboxylic acid-2-isopropylanilide; m.p.: 99°-101° C. (Compound No. 2.62).

The invention further relates to the use of 2-aminobiphenyl derivatives of the general formula II ##STR10## where the substituents have the following meanings: ##STR11## X methylene, sulfur, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine,

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen for combating Botrytis.

The compounds of the formula III are obtained for instance by reacting a correspondingly substituted carboxylic halide of the formula 4 ##STR12##

Hal denoting chlorine or bromine, with an ortho-substituted aniline of the formula 5 in the presence of a base. The carboxylic acids and their halides of the formula 4 are known. Some of the anilines of the formula 5 are known or can be prepared by known processes (Tetrahedron Letters, Vol. 28 p. 5093 (1987); THL Vol 295463 (1988)).

                                      TABLE 3                                      __________________________________________________________________________     No. A R.sup.1                                                                           R.sup.2                                                                          R.sup.3                                                                          R.sup.4                                                                           R.sup.5                                                                           R.sup.6                                                                           R.sup.7                                                                          R.sup.8                                                                             X  Phys. data [°C.]                        __________________________________________________________________________     3.1 A.sub.1                                                                          CH.sub.3                                                                          --                                                                               --                                                                               -- -- -- --                                                                               2-F  --                                                3.2 A.sub.1                                                                          CH.sub.3                                                                          --                                                                               --                                                                               -- -- -- --                                                                               4-F  --                                                3.3 A.sub.1                                                                          CF.sub.3                                                                          --                                                                               --                                                                               -- -- -- --                                                                               2-F  --                                                3.4 A.sub.1                                                                          CF.sub.3                                                                          --                                                                               --                                                                               -- -- -- --                                                                               4-F  --                                                3.5 A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               2-F  --                                                3.6 A.sup.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               2-CH.sub.3                                                                          -- 71-73                                          3.7 A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               2-Cl --                                                3.8 A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               2-OCH.sub.3                                                                         --                                                3.9 A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-F  --                                                3.10                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-Cl -- 95-98                                          3.11                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-CH.sub.3                                                                          --                                                3.12                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-OCH.sub.3                                                                         --                                                3.13                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-OiC.sub.3 H.sub.7                                                                 --                                                3.14                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               3-Br --                                                3.15                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               4-F  -- 156-157                                        3.16                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               4-Cl --                                                3.17                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               4-CH.sub.3                                                                          --                                                3.18                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               4-OCH.sub.3                                                                         --                                                3.19                                                                               A.sub.2                                                                          -- Cl                                                                               --                                                                               -- -- -- --                                                                               4-SCH.sub.3                                                                         --                                                3.20                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               2-F  CH.sub.2                                          3.21                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-F  CH.sub.2                                          3.22                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               4-F  CH.sub.2                                          3.23                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-Cl CH.sub.2                                          3.24                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-CH.sub.3                                                                          CH.sub.2                                          3.25                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               2-F  S                                                 3.26                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-F  S                                                 3.27                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               4-F  S                                                 3.28                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-Cl S                                                 3.29                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-CH.sub.3                                                                          S                                                 3.30                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               2-F  SO.sub.2                                          3.31                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-F  SO.sub.2                                          3.32                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               4-F  SO.sub.2                                          3.33                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-Cl SO.sub.2                                          3.34                                                                               A.sub.3                                                                          -- --                                                                               --                                                                               -- -- -- --                                                                               3-CH.sub.3                                                                          SO.sub.2                                          3.35                                                                               A.sub.5                                                                          -- --                                                                               --                                                                               CF.sub.3                                                                          CH.sub.3                                                                          -- --                                                                               2-F  --                                                3.36                                                                               A.sub.5                                                                          -- --                                                                               --                                                                               CF.sub.3                                                                          CH.sub.3                                                                          -- --                                                                               3-F  --                                                3.37                                                                               A.sub.5                                                                          -- --                                                                               --                                                                               CF.sub.3                                                                          CH.sub.3                                                                          -- --                                                                               4-F  --                                                3.38                                                                               A.sub.7                                                                          -- --                                                                               --                                                                               -- -- CH.sub.3                                                                          Cl                                                                               2-F  --                                                3.39                                                                               A.sub.7                                                                          -- --                                                                               --                                                                               -- -- CH.sub.3                                                                          Cl                                                                               3-F  --                                                3.40                                                                               A.sub.7                                                                          -- --                                                                               --                                                                               -- -- CH.sub.3                                                                          Cl                                                                               4-F  --                                                3.41                                                                               A.sub.7                                                                          -- --                                                                               --                                                                               -- -- CF.sub.3                                                                          Cl                                                                               2-F  --                                                3.42                                                                               A.sub.7                                                                          -- --                                                                               --                                                                               -- -- CF.sub.3                                                                          Cl                                                                               4-F  --                                                __________________________________________________________________________

The invention further relates to the use of 2-aminobiphenyl derivatives of the general formula IV ##STR13## where the substituents have the following meanings: ##STR14## X methylene, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine,

for combating Botrytis.

The compounds of the formula IV are obtained for example by reacting a corresponding aromatic or heterocyclic acid halide 4 with 2-aminobiphenyl 6 in the presence of a base. ##STR15##

Hal is chlorine or bromine.

The acids of the formula A-CO₂ H and their halides II are known.

                  TABLE 4                                                          ______________________________________                                          ##STR16##                                                                                                                       Phys.                                                                          data                         No.  A     R.sup.1                                                                               R.sup.2                                                                            R.sup.3                                                                             R.sup.4                                                                             R.sup.5                                                                             R.sup.6                                                                            R.sup.7                                                                            X    [°C.]                 ______________________________________                                         4.1  A.sub.1                                                                              CH.sub.3                                                                              --  --   --   --   --  --  --   87-88                        4.2  A.sub.1                                                                              Br     --  --   --   --   --  --  --   113-115                      4.3  A.sub.2                                                                              --     Cl  --   --   --   --  --  --   151-152                      4.4  A.sub.3                                                                              --     --  --   --   --   --  --  CH.sub.2                                                                            76-77                        4.5  A.sub.4                                                                              --     --  CH.sub.3                                                                            --   --   --  --  --   104-106                      4.6  A.sub.5                                                                              --     --  --   CH.sub.3                                                                            CH.sub. 3                                                                           --  --  --   136-137                      ______________________________________                                    

                                      TABLE 5                                      __________________________________________________________________________     No. A  R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.4                                                                           R.sup.5                                                                           R.sup.6                                                                            R.sup.7                                                                           X  Phys. data [°C.]                        __________________________________________________________________________     5.1 A.sub.1                                                                           CF.sub.3                                                                          -- -- -- -- --  -- -- 138-139                                        5.2 A.sub.1                                                                           J  -- -- -- -- --  -- -- 129-132                                        5.3 A.sub.1                                                                           -- CF.sub.3                                                                          -- -- -- --  -- --                                                5.4 A.sub.2                                                                           -- -- -- -- -- --  -- SO                                                5.5 A.sub.3                                                                           -- -- -- -- -- --  -- SO.sub.2                                          5.6 A.sub.5                                                                           -- -- -- CF.sub.3                                                                          CH.sub.3                                                                          --  -- -- 116-118                                        5.7 A.sub.6                                                                           -- -- -- CH.sub.3                                                                          CH.sub.3                                                                          --  -- --                                                5.8 A.sub.6                                                                           -- -- -- Cl Cl --  -- --                                                5.9 A.sub.7                                                                           -- -- -- -- -- CH.sub.3                                                                           Cl -- 108-109                                        5.10                                                                               A.sub.7                                                                           -- -- -- -- -- CF.sub.3                                                                           Cl --                                                5.11                                                                               A.sub.7                                                                           -- -- -- -- -- CH.sub.3                                                                           CH.sub.3                                                                          --                                                5.11                                                                               A.sub.1                                                                           Cl -- -- -- -- --     -- 100-103                                        __________________________________________________________________________

The invention further relates to the use of carboxanilide derivatives of the general formula V ##STR17## where the substituents have the following meanings: ##STR18## n 1 or 2 R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine,

R⁵ methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

                  TABLE 6                                                          ______________________________________                                         Compounds of the formula I where A is A.sub.1                                   ##STR19##                                                                                                       Phys. data                                   No.    R.sup.1 R.sup.7            mp [°C.]                              ______________________________________                                         6.1    CF.sub.3                                                                               i-C.sub.3 H.sub.7  160-162                                      6.2    CF.sub.3                                                                               n-C.sub.3 H.sub.7  151-152                                      6.3    CF.sub.3                                                                               n-C.sub.4 H.sub.9                                               6.4    CF.sub.3                                                                               sec.-C.sub.4 H.sub.9                                                                              83-84                                        6.5    CF.sub.3                                                                               i-C.sub.4 H.sub.9  133-135                                      6.6    CF.sub.3                                                                               tert.-C.sub.4 H.sub.9                                           6.7    CF.sub.3                                                                               n-C.sub.5 H.sub.11                                              6.8    CF.sub.3                                                                               sec.-C.sub.5 H.sub.11                                           6.9    CF.sub.3                                                                               n-C.sub.6 H.sub.13                                              6.10   CF.sub.3                                                                               n-C.sub.7 H.sub.15                                              6.11   CF.sub.3                                                                               sec.-C.sub.7 H.sub.15                                           6.12   CF.sub.3                                                                               1-Methylvinyl                                                   6.13   CF.sub.3                                                                               2-Methylvinyl                                                   6.14   CF.sub.3                                                                               Allyl                                                           6.15   CF.sub.3                                                                               2-Methylallyl                                                   6.16   CF.sub.3                                                                               2-Ethylallyl                                                    6.17   CF.sub.3                                                                               1-Methylallyl                                                   6.18   CF.sub.3                                                                               1-Ethylallyl                                                    6.19   CF.sub.3                                                                               1-Methyl-2-butenyl                                              6.20   CF.sub.3                                                                               1-Ethyl-2-butenyl                                               6.21   CF.sub.3                                                                               1-Isopropyl-2-butenyl                                           6.22   CF.sub.3                                                                               1-n-Butyl-2-butenyl                                             6.23   CF.sub.3                                                                               1-Methyl-2-pentenyl                                             6.24   CF.sub.3                                                                               1,4-Dimethyl-2-pentenyl                                         6.25   CF.sub.3                                                                               Propargyl                                                       6.26   CF.sub.3                                                                               2-butynyl                                                       6.27   CF.sub.3                                                                               3-butynyl                                                       6.28   CF.sub.3                                                                               Ethoxy                                                          6.29   CF.sub.3                                                                               Propoxy                                                         6.30   CF.sub.3                                                                               1-Methylethoxy                                                  6.31   CF.sub.3                                                                               n-Butoxy                                                        6.32   CF.sub.3                                                                               1-Methylpropoxy                                                 6.33   CF.sub.3                                                                               2-Methylpropoxy                                                 6.34   CF.sub.3                                                                               1,1-Dimethylethoxy                                              6.35   CF.sub.3                                                                               n-Pentyloxy                                                     6.36   CF.sub.3                                                                               n-Hexyloxy                                                      6.37   CF.sub.3                                                                               2-Ethylhexyloxy                                                 6.38   CF.sub.3                                                                               2-Propenyloxy                                                   6.39   CF.sub.3                                                                               2-Butentyloxy                                                   6.40   CF.sub.3                                                                               2-Methyl-2-propenyloxy                                          6.41   CF.sub.3                                                                               2-Pentenyloxy                                                   6.42   CF.sub.3                                                                               3-Pentenyloxy                                                   6.43   CF.sub.3                                                                               3-chloro-2-propenyloxy                                          6.44   CF.sub.3                                                                               2,3-Dichloro-2-propenyloxy                                      6.45   CF.sub.3                                                                               2,3,3-Trichloro-propenyloxy                                     6.46   CF.sub.3                                                                               2-propynyloxy                                                   6.47   CF.sub.3                                                                               2-butynyl-oxy                                                   6.48   CF.sub.3                                                                               3-butynyl-oxy                                                   6.49   CF.sub.3                                                                               1-Methyl-2-propynyloxy                                          6.50   CF.sub.3                                                                               Cyclopropyl                                                     6.51   CF.sub.3                                                                               Cyclobutyl                                                      6.52   CF.sub.3                                                                               Cyclopentyl        150-152                                      6.53   CF.sub.3                                                                               Cyclohexyl         130-132                                      6.54   CF.sub.3                                                                               2-Cyclopentenyl    160-161                                      6.55   CF.sub.3                                                                               1-Cyclopentenyl                                                 6.56   CF.sub.3                                                                               2-Cyclohexenyl     103-105                                      6.57   CF.sub.3                                                                               1-Cyclohexenyl                                                  6.58   CF.sub.3                                                                               Cyclopentyloxy                                                  6.59   CF.sub.3                                                                               Cyclohexyloxy                                                   6.60   CF.sub.3                                                                               2-Cyclopentenyloxy                                              6.61   CF.sub.3                                                                               2-Cyclohexenyloxy                                               ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                         Compounds of the formula V where A is A.sub.1                                   ##STR20##                                                                                                       Phys. data                                   No.     R.sup.1                                                                               R.sup.7            mp [°C.]                              ______________________________________                                         7.1     Cl     i-C.sub.3 H.sub.7  125-127                                      7.2     Cl     n-C.sub.3 H.sub.7  108-110                                      7.3     Cl     n-C.sub.4 H.sub.9                                               7.4     Cl     sec.-C.sub.4 H.sub.9                                                                              73-74                                        7.5     Cl     i-C.sub.4 H.sub.9  90-92                                        7.6     Cl     tert.-C.sub.4 H.sub.9                                           7.7     Cl     n-C.sub.5 H.sub.11                                              7.8     Cl     sec.-C.sub.5 H.sub.11                                           7.9     Cl     n-C.sub.6 H.sub.13                                              7.10    Cl     n-C.sub.7 H.sub.15                                              7.11    Cl     sec.-C.sub.7 H.sub.15                                           7.12    Cl     1-Methylvinyl                                                   7.13    Cl     2-Methylvinyl                                                   7.14    Cl     Allyl                                                           7.15    Cl     2-Methylally                                                    7.16    Cl     2-Ethylallyl                                                    7.17    Cl     1-Methylallyl                                                   7.18    Cl     1-Ethylallyl                                                    7.19    Cl     1-Methyl-2-butenyl                                              7.20    Cl     1-Ethyl-2-butenyl                                               7.21    Cl     1-Isopropyl-2-butenyl                                           7.22    Cl     1-n-Butyl-2-butenyl                                             7.23    Cl     1-Methyl-2-pentenyl                                             7.24    Cl     1,4-Dimethyl-2-pentenyl                                         7.25    Cl     Propargyl                                                       7.26    Cl     2-butynyl                                                       7.27    Cl     3-butynyl                                                       7.28    Cl     Ethoxy                                                          7.29    Cl     Propoxy                                                         7.30    Cl     1-Methylethoxy                                                  7.31    Cl     n-Butoxy                                                        7.32    Cl     1-Methylpropoxy                                                 7.33    Cl     2-Methylpropoxy                                                 7.34    Cl     1,1-Dimethylethoxy                                              7.35    Cl     n-Pentyloxy                                                     7.36    Cl     n-Hexyloxy                                                      7.37    Cl     2-Ethylhexyloxy                                                 7.38    Cl     2-Propenyloxy                                                   7.39    Cl     2-Butentyloxy                                                   7.40    Cl     2-Methyl-2-propenyloxy                                          7.41    Cl     2-Pentenyloxy                                                   7.42    Cl     3-Pentenyloxy                                                   7.43    Cl     3-chloro-2-propenyloxy                                          7.44    Cl     2,3-Dichloro-2-propenyloxy                                      7.45    Cl     2,3,3-Trichloro-propenyloxy                                     7.46    Cl     2-propynyloxy                                                   7.47    Cl     2-butynyl-oxy                                                   7.48    Cl     3-butynyl-oxy                                                   7.49    Cl     1-Methyl-2-propynyloxy                                          7.50    Cl     Cyclopropyl                                                     7.51    Cl     Cyclobutyl                                                      7.52    Cl     Cyclopentyl        110-111                                      7.53    Cl     Cyclohexyl         141-142                                      7.54    Cl     2-Cyclopentenyl    110-112                                      7.55    Cl     1-Cyclopentenyl                                                 7.56    Cl     2-Cyclohexenyl     84-86                                        7.57    Cl     1-Cyclohexenyl                                                  7.58    Cl     Cyclopentyloxy                                                  7.59    Cl     Cyclohexyloxy                                                   7.60    Cl     2-Cyclopentenyloxy                                              7.61    Cl     2-Cyclohexenyloxy                                               ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                         Compounds of the formula V where A is A.sub.2                                   ##STR21##                                                                                                       Phys. data                                   No.     n      R.sup.7            mp [°C.]                              ______________________________________                                         8.1     2      i-C.sub.3 H.sub.7                                               8.2     2      n-C.sub.3 H.sub.7                                               8.3     2      n-C.sub.4 H.sub.9                                               8.4     2      sec.-C.sub.4 H.sub.9                                                                              96-98                                        8.5     2      i-C.sub.4 H.sub.9  85-86                                        8.6     2      tert.-C.sub.4 H.sub.9                                           8.7     2      n-C.sub.5 H.sub.11                                              8.8     2      sec.-C.sub.5 H.sub.11                                           8.9     2      n-C.sub.6 H.sub.13                                              8.10    2      n-C.sub.7 H.sub.15                                              8.11    2      sec.-C.sub.7 H.sub.15                                           8.12    2      1-Methylvinyl                                                   8.13    2      2-Methylvinyl                                                   8.14    2      Allyl                                                           8.15    2      2-Methylallyl                                                   8.16    2      2-Ethylallyl                                                    8.17    2      1-Methylallyl                                                   8.18    2      1-Ethylallyl                                                    8.19    2      1-Methyl-2-butenyl                                              8.20    2      1-Ethyl-2-butenyl                                               8.21    2      1-Isopropyl-2-butenyl                                           8.22    2      1-n-Butyl-2-butenyl                                             8.23    2      1-Methyl-2-pentenyl                                             8.24    2      1,4-Dimethyl-2-pentenyl                                         8.25    2      Propargyl                                                       8.26    2      2-butynyl                                                       8.27    2      3-butynyl                                                       8.28    2      Ethoxy                                                          8.29    2      Propoxy                                                         8.30    2      1-Methylethoxy                                                  8.31    2      n-Butoxy                                                        8.32    2      1-Methylpropoxy    100-102                                      8.33    2      2-Methylpropoxy                                                 8.34    2      1,1-Dimethylethoxy                                              8.35    2      n-Pentyloxy                                                     8.36    2      n-Hexyloxy                                                      8.37    2      2-Ethylhexyloxy                                                 8.38    2      2-Propenyloxy                                                   8.39    2      2-Butentyloxy                                                   8.40    2      2-methyl-2-propenyloxy                                          8.41    2      2-Pentenyloxy                                                   8.42    2      3-Pentenyloxy                                                   8.43    2      3-chloro-2-propenyloxy                                          8.44    2      2,3-Dichloro-2-propenyloxy                                      8.45    2      2,3,3-Trichloro-propenyloxy                                     8.46    2      2-propynyloxy                                                   8.47    2      2-butynyl-oxy                                                   8.48    2      3-butynyl-oxy                                                   8.49    2      1-Methyl-2-propynyloxy                                          8.50    2      Cyclopropyl                                                     8.51    2      Cyclobutyl                                                      8.52    2      Cyclopentyl        128-130                                      8.53    2      Cyclohexyl         134-135                                      8.54    2      2-Cyclopentenyl                                                 8.55    2      1-Cyclopentenyl                                                 8.56    2      2-Cyclohexenyl                                                  8.57    2      1-Cyclohexenyl                                                  8.58    2      Cyclopentyloxy                                                  8.59    2      Cyclohexyloxy                                                   8.60    2      2-Cyclopentenyloxy                                              8.61    2      2-Cyclohexenyloxy                                               8.62    1      i-C.sub.3 H.sub.7                                               8.63    1      n-C.sub.3 H.sub.7                                               8.64    1      n-C.sub.4 H.sub.9                                               8.65    1      sec.-C.sub.4 H.sub.9                                                                              oil                                          8.66    1      i-C.sub.4 H.sub.9  oil                                          8.67    1      tert.-C.sub.4 H.sub.9                                           8.68    1      n-C.sub.5 H.sub.11                                              8.69    1      sec.-C.sub.5 H.sub.11                                           8.70    1      n-C.sub.6 H.sub.13                                              8.71    1      n-C.sub.7 H.sub.15                                              8.72    1      sec.-C.sub.7 H.sub.15                                           8.73    1      Ethoxy                                                          8.74    1      Propoxy                                                         8.75    1      1-Methylethoxy                                                  8.76    1      n-Butoxy                                                        8.77    1      1-Methylpropoxy                                                 8.78    1      2-Methylpropoxy                                                 8.79    1      1,1-Dimethylethoxy                                              8.80    1      n-Pentyloxy                                                     8.81    1      n-Hexyloxy                                                      8.82    1      Cyclopentyl                                                     ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         Compounds of the formula V where A is A.sub.4                                   ##STR22##                                                                                                         Phys. data                                 No.   R.sup.3                                                                               R.sup.4                                                                               R.sup.7         mp [°C.]                            ______________________________________                                         9.1   CF.sub.3                                                                              CH.sub.3                                                                              i-C.sub.3 H.sub.7                                                                              115-116                                    9.2   CF.sub.3                                                                              CH.sub.3                                                                              n-C.sub.3 H.sub.7                                                                              114-116                                    9.3   CF.sub.3                                                                              CH.sub.3                                                                              n-C.sub.4 H.sub.9                                          9.4   CF.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.4 H.sub.9                                                                           73-75                                      9.5   CF.sub.3                                                                              CH.sub.3                                                                              i-C.sub.4 H.sub.9                                                                              100-102                                    9.6   CF.sub.3                                                                              CH.sub.3                                                                              tert-C.sub.4 H.sub.9                                       9.7   CF.sub.3                                                                              CH.sub.3                                                                              n-C.sub.5 H.sub.11                                         9.8   CF.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.5 H.sub.11                                      9.9   CF.sub.3                                                                              CH.sub.3                                                                              n-CH.sub.6 H.sub.1                                         9.10  CF.sub.3                                                                              CH.sub.3                                                                              n-C.sub.7 H.sub.15                                         9.11  CF.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.7 H.sub.15                                      9.12  CF.sub.3                                                                              CH.sub.3                                                                              1-Methylvinyl                                              9.13  CF.sub.3                                                                              CH.sub.3                                                                              2-Methylvinyl                                              9.14  CF.sub.3                                                                              CH.sub.3                                                                              Allyl                                                      9.15  CF.sub.3                                                                              CH.sub.3                                                                              2-Methylallyl                                              9.16  CF.sub.3                                                                              CH.sub.3                                                                              2-Ethylallyl                                               9.17  CF.sub.3                                                                              CH.sub.3                                                                              1-Methylallyl                                              9.18  CF.sub.3                                                                              CH.sub.3                                                                              1-Ethylallyl                                               9.19  CF.sub.3                                                                              CH.sub.3                                                                              1-Methyl-2-butenyl                                         9.20  CF.sub.3                                                                              CH.sub.3                                                                              1-Ethyl-2-butenyl                                          9.21  CF.sub.3                                                                              CH.sub.3                                                                              1-Isopropyl-2-butenyl                                      9.22  CF.sub.3                                                                              CH.sub.3                                                                              1-n-Butyl-2-butenyl                                        9.23  CF.sub.3                                                                              CH.sub.3                                                                              1-Methyl-2-pentenyl                                        9.24  CF.sub.3                                                                              CH.sub.3                                                                              1,4-Dimethyl-2-pentenyl                                    9.25  CF.sub.3                                                                              CH.sub.3                                                                              Propargyl                                                  9.26  CF.sub.3                                                                              CH.sub.3                                                                              2-butynyl                                                  9.27  CF.sub.3                                                                              CH.sub.3                                                                              3-butynyl                                                  9.28  CF.sub.3                                                                              CH.sub.3                                                                              Ethoxy                                                     9.29  CF.sub.3                                                                              CH.sub.3                                                                              Propoxy                                                    9.30  CF.sub.3                                                                              CH.sub.3,                                                                             1-Methylethoxy                                             9.31  CF.sub.3                                                                              CH.sub.3                                                                              n-Butoxy                                                   9.32  CF.sub.3                                                                              CH.sub.3                                                                              1-Methylpropoxy                                            9.33  CF.sub.3                                                                              CH.sub.3                                                                              2-Methylpropoxy                                            9.34  CF.sub.3                                                                              CH.sub.3                                                                              1,1-Dimethylethoxy                                         9.35  CF.sub.3                                                                              CH.sub.3                                                                              n-Pentyloxy                                                9.36  CF.sub.3                                                                              CH.sub.3                                                                              n-Hexyloxy                                                 9.37  CF.sub.3                                                                              CH.sub.3                                                                              2-Ethylhexyloxy                                            9.38  CF.sub.3                                                                              CH.sub.3                                                                              2-Propenyloxy                                              9.39  CF.sub.3                                                                              CH.sub.3                                                                              2-Butentyloxy                                              9.40  CF.sub.3                                                                              CH.sub.3                                                                              2-Methyl-2-propenyloxy                                     9.41  CF.sub.3                                                                              CH.sub.3                                                                              2-Pentenyloxy                                              9.42  CF.sub.3                                                                              CH.sub.3                                                                              3-Pentenyloxy                                              9.43  CF.sub.3                                                                              CH.sub.3                                                                              3-chloro-2-propenyloxy                                     9.44  CF.sub.3                                                                              CH.sub.3                                                                              2,3-Dichloro-2-propenyloxy                                 9.45  CF.sub.3                                                                              CH.sub.3                                                                              2,3,3-Trichloro-propenyloxy                                9.46  CF.sub.3                                                                              CH.sub.3                                                                              2-propynyloxy                                              9.47  CF.sub.3                                                                              CH.sub.3                                                                              2-butynyl-oxy                                              9.48  CF.sub.3                                                                              CH.sub.3                                                                              3-butynyl-oxy                                              9.49  CF.sub.3                                                                              CH.sub.3                                                                              1-Methyl-2-propynyloxy                                     9.50  CF.sub.3                                                                              CH.sub.3                                                                              Cyclopropyl                                                9.51  CF.sub.3                                                                              CH.sub.3                                                                              Cyclobutyl                                                 9.52  CF.sub.3                                                                              CH.sub.3                                                                              Cyclopentyl     114-118                                    9.53  CF.sub.3                                                                              CH.sub.3                                                                              Cyclohexyl      100-104                                    9.54  CF.sub.3                                                                              CH.sub.3                                                                              2-Cyclopentenyl 116-120                                    9.55  CF.sub.3                                                                              CH.sub.3                                                                              1-Cyclopentenyl                                            9.56  CF.sub.3                                                                              CH.sub.3                                                                              2-Cyclohexenyl  96-98                                      9.57  CF.sub.3                                                                              CH.sub.3                                                                              1-Cyclohexenyl                                             9.58  CF.sub.3                                                                              CH.sub.3                                                                              Cyclopentyloxy                                             9.59  CF.sub.3                                                                              CH.sub.3                                                                              Cyclohexyloxy                                              9.60  CF.sub.3                                                                              CH.sub.3                                                                              2-Cyclopentenyloxy                                         9.61  CF.sub.3                                                                              CH.sub.3                                                                              2-Cyclohexenyloxy                                          9.62  CH.sub.3                                                                              CH.sub.3                                                                              i-C.sub.3 H.sub.7                                          9.63  CH.sub.3                                                                              CH.sub.3                                                                              n-C.sub.3 H.sub.7                                          9.64  CH.sub.3                                                                              CH.sub.3                                                                              n-C.sub.4 H.sub.9                                          9.65  CH.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.4 H.sub.9                                                                           136                                        9.66  CH.sub.3                                                                              CH.sub.3                                                                              i-C.sub.4 H.sub.9                                                                              96-97                                      9.67  CH.sub.3                                                                              CH.sub.3                                                                              tert.-C.sub.4 H.sub.9                                      9.68  CH.sub.3                                                                              CH.sub.3                                                                              n-C.sub.5 H.sub.11                                         9.69  CH.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.5 H.sub.11                                      9.70  CH.sub.3                                                                              CH.sub.3                                                                              n-C.sub.6 H.sub.13                                         9.71  CH.sub.3                                                                              CH.sub.3                                                                              n-C.sub.7 H.sub.15                                         9.72  CH.sub.3                                                                              CH.sub.3                                                                              sec.-C.sub.7 H.sub.15                                      9.73  CH.sub.3                                                                              CH.sub.3                                                                              Ethoxy                                                     9.74  CH.sub.3                                                                              CH.sub.3                                                                              Propoxy                                                    9.75  CH.sub.3                                                                              CH.sub.3                                                                              1-Methylethoxy                                             9.76  CH.sub.3                                                                              CH.sub.3                                                                              n-Butoxy                                                   9.77  CH.sub.3                                                                              CH.sub.3                                                                              1-Methylpropoxy                                            9.78  CH.sub.3                                                                              CH.sub.3                                                                              2-Methylpropoxy                                            9.79  CH.sub.3                                                                              CH.sub.3                                                                              1,1-Dimethylethoxy                                         9.80  CH.sub.3                                                                              CH.sub.3                                                                              n-Pentyloxy                                                9.81  CH.sub.3                                                                              CH.sub.3                                                                              n-Hexyloxy                                                 9.82  CH.sub.3                                                                              CH.sub.3                                                                              Cyclopentyl     128-130                                    9.83  CH.sub.3                                                                              CH.sub.3                                                                              Cyclopentenyl   128-129                                    9.84  CH.sub.3                                                                              CH.sub.3                                                                              Cyclohexyl      128-129                                    9.85  CH.sub.3                                                                              CH.sub.3                                                                              1-Ethyl-propoxy 45-47                                      9.86  CH.sub.3                                                                              CH.sub.3                                                                              Cyclopentyloxy  97-99                                      9.87  CH.sub.3                                                                              CH.sub.3                                                                              2-Cyclohexenyloxy                                                                              87-89                                      9.88  CH.sub.3                                                                              CH.sub.3                                                                              2-Methyl-2-propenyloxy                                                                         103-105                                    ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.6                                   ##STR23##                                                                                                         Phys. data                                 No.   R.sup.5                                                                               R.sup.6                                                                               R.sup.7         mp [°C.]                            ______________________________________                                         10.1  CH.sub.3                                                                              Cl     i-C.sub.3 H.sub.7                                                                              108-110                                    10.2  CH.sub.3                                                                              Cl     n-C.sub.3 H.sub.7                                                                              129-130                                    10.3  CH.sub.3                                                                              Cl     n-C.sub.4 H.sub.9                                          10.4  CH.sub.3                                                                              Cl     sec.-C.sub.4 H.sub.9                                                                           71-73                                      10.5  CH.sub.3                                                                              Cl     i-C.sub.4 H.sub.9                                                                              119-120                                    10.6  CH.sub.3                                                                              Cl     tert-C.sub.4 H.sub.9                                       10.7  CH.sub.3                                                                              Cl     n-C.sub.5 H.sub.11                                         10.8  CH.sub.3                                                                              Cl     sec.-C.sub.5 H.sub.11                                      10.9  CH.sub.3                                                                              Cl     n-C.sub.6 H.sub.13                                         10.10 CH.sub.3                                                                              Cl     n-C.sub.7 H.sub.15                                         10.11 CH.sub.3                                                                              Cl     sec.-C.sub.7 H.sub.15                                      10.12 CH.sub.3                                                                              Cl     1-Methylvinyl                                              10.13 CH.sub.3                                                                              Cl     2-Methylvinyl                                              10.14 CH.sub.3                                                                              Cl     Allyl                                                      10.15 CH.sub.3                                                                              Cl     2-Methylallyl                                              10.16 CH.sub.3                                                                              Cl     2-Ethylallyl                                               10.17 CH.sub.3                                                                              Cl     1-Methylallyl                                              10.18 CH.sub.3                                                                              Cl     l-Ethylallyl                                               10.19 CH.sub.3                                                                              Cl     1-Methyl-2-butenyl                                         10.20 CH.sub.3                                                                              Cl     1-Ethyl-2-butenyl                                          10.21 CH.sub.3                                                                              Cl     1-Isopropyl-2-butenyl                                      10.22 CH.sub.3                                                                              Cl     1-n-Butyl-2-butenyl                                        10.23 CH.sub.3                                                                              Cl     1-Methyl-2-pentenyl                                        10.24 CH.sub.3                                                                              Cl     1,4-Dimethyl-2-pentenyl                                    10.25 CH.sub.3                                                                              Cl     Propargyl                                                  10.26 CH.sub.3                                                                              Cl     2-butynyl                                                  10.27 CH.sub.3                                                                              Cl     3-butynyl                                                  10.28 CH.sub.3                                                                              Cl     Ethoxy                                                     10.29 CH.sub.3                                                                              Cl     Propoxy                                                    10.30 CH.sub.3                                                                              Cl     1-Methylethoxy                                             10.31 CH.sub.3                                                                              Cl     n-Butoxy                                                   10.32 CH.sub.3                                                                              Cl     1-Methylpropoxy                                            10.33 CH.sub.3                                                                              Cl     2-Methylpropoxy                                            10.34 CH.sub.3                                                                              Cl     1,1-Dimethylethoxy                                         10.35 CH.sub.3                                                                              Cl     n-Pentyloxy                                                10.36 CH.sub.3                                                                              Cl     n-Hexyloxy                                                 10.37 CH.sub.3                                                                              Cl     2-Ethylhexyloxy                                            10.38 CH.sub.3                                                                              Cl     2-Propenyloxy                                              10.39 CH.sub.3                                                                              Cl     2-Butentyloxy                                              10.40 CH.sub.3                                                                              Cl     2-methyl-2-propenyloxy                                     10.41 CH.sub.3                                                                              Cl     2-Pentenyloxy                                              10.42 CH.sub.3                                                                              Cl     3-Pentenyloxy                                              10.43 CH.sub.3                                                                              Cl     3-chloro-2-propenyloxy                                     10.44 CH.sub.3                                                                              Cl     2,3-Dichloro-2-propenyloxy                                 10.45 CH.sub.3                                                                              Cl     2,3,3-Trichloro-propenyloxy                                10.46 CH.sub.3                                                                              Cl     2-propynyloxy                                              10.47 CH.sub.3                                                                              Cl     2-butynyl-oxy                                              10.48 CH.sub.3                                                                              Cl     3-butynyl-oxy                                              10.49 CH.sub.3                                                                              Cl     1-Methyl-2-propynyloxy                                     10.50 CH.sub.3                                                                              Cl     Cyclopropyl                                                10.51 CH.sub.3                                                                              Cl     Cyclobutyl                                                 10.52 CH.sub.3                                                                              Cl     Cyclopentyl     122-123                                    10.53 CH.sub.3                                                                              Cl     Cyclohexyl      143-144                                    10.54 CH.sub.3                                                                              Cl     2-Cyclopentenyl 123-125                                    10.55 CH.sub.3                                                                              Cl     1-Cyclopentenyl                                            10.56 CH.sub.3                                                                              Cl     2-Cyclohexenyl  114-116                                    10.57 CH.sub.3                                                                              Cl     1-Cyclohexenyl                                             10.58 CH.sub.3                                                                              Cl     Cyclopentyloxy                                             10.59 CH.sub.3                                                                              Cl     Cyclohexyloxy                                              10.60 CH.sub.3                                                                              Cl     2-Cyclopentenyloxy                                         10.61 CH.sub.3                                                                              Cl     2-Cyclohexenyloxy                                          10.62 CF.sub.3                                                                              Cl     i-C.sub.3 H.sub.7                                          10.63 CF.sub.3                                                                              Cl     n-C.sub.3 H.sub.7                                          10.64 CF.sub.3                                                                              Cl     n-C.sub.4 H.sub.9                                          10.65 CF.sub.3                                                                              Cl     sec.-C.sub.4 H.sub.9                                                                           108-110                                    10.66 CF.sub.3                                                                              Cl     i-C.sub.4 H.sub.9                                                                              122-124                                    10.67 CF.sub.3                                                                              Cl     tert.-C.sub.4 H.sub.9                                      10.68 CF.sub.3                                                                              Cl     n-C.sub.5 H.sub.11                                         10.69 CF.sub.3                                                                              Cl     sec.-C.sub.5 H.sub.11                                      10.70 CF.sub.3                                                                              Cl     n-C.sub.6 H.sub.13                                         10.71 CF.sub.3                                                                              Cl     n-C.sub.7 H.sub.15                                         10.72 CF.sub.3                                                                              Cl     sec.-C.sub.7 H.sub.15                                      10.73 CF.sub.3                                                                              Cl     Ethoxy                                                     10.74 CF.sub.3                                                                              Cl     Propoxy                                                    10.75 CF.sub.3                                                                              Cl     1-Methylethoxy                                             10.76 CF.sub.3                                                                              Cl     n-Butoxy                                                   10.77 CF.sub.3                                                                              Cl     1-Methylpropoxy                                            10.78 CF.sub.3                                                                              Cl     2-Methylpropoxy                                            10.79 CF.sub.3                                                                              Cl     1,1-Dimethylethoxy                                         10.80 CF.sub.3                                                                              Cl     n-Pentyloxy                                                10.81 CF.sub.3                                                                              Cl     n-Hexyloxy                                                 10.82 CF.sub.3                                                                              Cl     Cyclopentyl     113-115                                    10.83 CF.sub.3                                                                              Cl     Cyclopentenyl   132-133                                    ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.7                                   ##STR24##                                                                                                        Phys. data                                  No.     R.sup.2                                                                               R.sup.6 R.sup.7     mp [°C.]                             ______________________________________                                         11.1    H      CH.sub.3                                                                               i-C.sub.3 H.sub.7                                       11.2    H      CH.sub.3                                                                               n-C.sub.3 H.sub.7                                       11.3    H      CH.sub.3                                                                               n-C.sub.4 H.sub.9                                       11.4    H      CH.sub.3                                                                               sec.-C.sub.4 H.sub.9                                                                       oil                                         11.5    H      CH.sub.3                                                                               i-C.sub.4 H.sub.9                                                                          oil                                         11.6    H      CH.sub.3                                                                               tert.-C.sub.4 H.sub.9                                   11.7    H      CH.sub.3                                                                               n-C.sub.5 H.sub.11                                      11.8    H      CH.sub.3                                                                               sec.-C.sub.5 H.sub.11                                   11.9    H      CH.sub.3                                                                               n-C.sub.6 H.sub.13                                      11.10   H      CH.sub.3                                                                               n-C.sub.7 H.sub.15                                      11.11   H      CH.sub.3                                                                               sec.-C.sub.7 H.sub.15                                   11.12   H      CH.sub.3                                                                               Ethoxy                                                  11.13   H      CH.sub.3                                                                               Propoxy                                                 11.14   H      CH.sub.3                                                                               1-Methylethoxy                                          11.15   H      CH.sub.3                                                                               n-Butoxy                                                11.16   H      CH.sub.3                                                                               1-Methylpropoxy                                         11.17   H      CH.sub.3                                                                               2-Methylpropoxy                                         11.18   H      CH.sub.3                                                                               1,1-Dimethylethoxy                                      11.19   H      CH.sub.3                                                                               n-Pentyloxy                                             11.20   H      CH.sub.3                                                                               n-Hexyloxy                                              11.21   H      CH.sub.3                                                                               Cyclopentyl                                             11.22   H      CH.sub.3                                                                               Cyclopentenyl                                           ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.3                                   ##STR25##                                                                                                     Phys. data                                     No      R.sup.2 R.sup.7         mp [°C.]                                ______________________________________                                         12.1    H       i-C.sub.3 H.sub.7                                                                              147-148                                        12.2    H       n-C.sub.3 H.sub.7                                              12.3    H       n-C.sub.4 H.sub.9                                              12.4    H       sec.-C.sub.4 H.sub.9                                                                           109-110                                        12.5    H       i-C.sub.4 H.sub.9                                                                              114-115                                        12.6    H       tert.-C.sub.4 H.sub.9                                          12.7    H       n-C.sub.5 H.sub.11                                             12.8    H       sec.-C.sub.5.sub.H.sub.11                                      12.9    H       n-C.sub.6 H.sub.13                                             12.10   H       n-C.sub.7 H.sub.15                                             12.11   H       sec.-C.sub.7 H.sub.15                                          12.12   H       Ethoxy                                                         12.13   H       Propoxy                                                        12.14   H       1-Methylethoxy                                                 12.15   H       n-Butoxy                                                       12.16   H       1-Methylpropoxy                                                12.17   H       2-Methylpropoxy                                                12.18   H       1,1-Dimethylethoxy                                             12.19   H       n-Pentyloxy                                                    12.20   H       n-Hexyloxy                                                     12.21   H       Cyclopentyl     97-98                                          12.22   H       Cyclohexyl      125-127                                        12.23   H       2-Cyclopentenyl 98-99                                          12.24   H       1-Cyclopentenyl                                                12.25   H       2-Cyclohexenyl  82-84                                          12.26   H       1-Cyclohexenyl                                                 12.27   H       Cyclopentyloxy  73-75                                          12.28   H       Cyclohexyloxy                                                  12.29   H       2-Cyclopentenyloxy                                             12.30   CH.sub.3                                                                               i-C.sub.3 H.sub.7                                              12.31   CH.sub.3                                                                               n-C.sub.3 H.sub.7                                              12.32   CH.sub.3                                                                               n-C.sub.4 H.sub.9                                              12.33   CH.sub.3                                                                               sec.-C.sub.4 H.sub.9                                                                           80-82                                          12.34   CH.sub.3                                                                               i-C.sub.4 H.sub.9                                                                              114-116                                        12.35   CH.sub.3                                                                               tert.-C.sub.4 H.sub.9                                          12.36   CH.sub.3                                                                               n-C.sub.5 H.sub.11                                             12.37   CH.sub.3                                                                               sec.-C.sub.4 H.sub.9                                           12.38   CH.sub.3                                                                               n-C.sub.6 H.sub.13                                             12.39   CH.sub.3                                                                               n-C.sub.7 H.sub.15                                             12.40   CH.sub.3                                                                               sec.-C.sub.7 H.sub.15                                          12.41   CH.sub.3                                                                               Ethoxy                                                         12.42   CH.sub.3                                                                               Propoxy                                                        12.43   CH.sub.3                                                                               1-Methylethoxy                                                 12.44   CH.sub.3                                                                               n-Butoxy                                                       12.45   CH.sub.3                                                                               1-Methylpropoxy                                                12.46   CH.sub.3                                                                               2-Methylpropoxy                                                12.47   CH.sub.3                                                                               1,1-Dimethylethoxy                                             12.48   CH.sub.3                                                                               n-Pentyloxy                                                    12.49   CH.sub.3                                                                               n-Hexyloxy                                                     12.50   CH.sub.3                                                                               Cyclopentyl                                                    12.51   H       2-Methyl-2-propenyloxy                                                                         40-41                                          12.52   H       1-Ethyl-propoxy oil                                            12.53   H       2-Cyclohexenyloxy                                                                              51-53                                          ______________________________________                                    

Manufacturing examples

Example 7

At 0° C., 2.3 g of 2-methyl-4-trifluoromethyl-thiazole-5-carboxylic chloride is dripped into a solution of 1.4 g of 2-n-propylaniline and 1.1 g of triethylamine in 15 ml of tetrahydrofuran, and the mixture is stirred for 12 hours at 20° C.

After dilution with 300 ml of water, extraction with methyltert.-butyl ether (2×70 ml), evaporation of the solvent and mixture of the residue with a small amount of n-pentane, there is isolated 2.8 g of 2-methyl-4-trifluoromethyl-thiazole-5-carboxylic acid-2-n-propyl-anilide; m.p.: 114°-116° C. (Table 9, No. 2).

Example 8

At 0° C., 3.8 g of 1,3-dimethyl-5-chloroopyrazole-4-carboxylic chloride is dripped into a solution of 2.7 g of 2-isopropylamine and 2.2 g of triethylamine in 40 ml of dichloromethane, and the mixture is stirred for 2 hours at 0° C.

After washing with 50 ml of water, evaporation of the solvent and recrystallization from cyclohexane there is isolated 3.3 g of 1,3-dimethyl-5-chloropyrazole-4-carboxylic acid-2-isopropylanilide; m.p. 108°-110° C. (Table 10, No. 1).

                  TABLE 13                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.1                                   ##STR26##                                                                                                      Phys. data                                    No.     R.sup.1                                                                               R.sup.7           mp [°C.]                               ______________________________________                                         13.1    Br     i-C.sub.3 H.sub.7                                               13.2    Br     n-C.sub.3 H.sub.7                                               13.3    Br     n-C.sub.4 H.sub.9                                               13.4    Br     sec.-C.sub.4 H.sub.9                                                                             74-75                                         13.5    Br     i-C.sub.4 H.sub.9 110-112                                       13.6    Br     tert.-C.sub.4 H.sub.9                                           13.7    Br     n-C.sub.4 H.sub.9                                               13.8    Br     sec.-.sub.5 H.sub.11                                            13.9    Br     n-C.sub.6 H.sub.13                                              13.10   Br     n-C.sub.7 H.sub.15                                              13.11   Br     sec.-C.sub.7 H.sub.15                                           13.12   Br     1-Methylvinyl                                                   13.13   Br     2-Methylvinyl                                                   13.14   Br     Allyl                                                           13.15   Br     2-Methylallyl                                                   13.16   Br     2-Ethylallyl                                                    13.17   Br     1-Methylallyl                                                   13.18   Br     I-Ethylallyl                                                    13.19   Br     1-Methyl-2-butenyl                                              13.20   Br     l-Ethyl-2-butenyl                                               13.21   Br     1-Isopropyl-2-butenyl                                           13.22   Br     1-n-Butyl-2-butenyl                                             13.23   Br     1-Methyl-2-pentenyl                                             13.24   Br     1,4-Dimethyl-2-pentenyl                                         13.25   Br     Propargyl                                                       13.26   Br     2-butynyl                                                       13.27   Br     3-butynyl                                                       13.28   Br     Ethoxy                                                          13.29   Br     Propoxy                                                         13.30   Br     1-Methylethoxy                                                  13.31   Br     n-Butoxy                                                        13.32   Br     1-methylpropoxy                                                 13.33   Br     2-Methylpropoxy                                                 13.34   Br     1,1-Dimethylethoxy                                              13.35   Br     n-Pentyloxy                                                     13.36   Br     n-Hexyloxy                                                      13.37   Br     2-Ethylhexyloxy                                                 13.38   Br     2-Propenyloxy                                                   13.39   Br     2-Butentyloxy                                                   13.40   Br     2-Methyl-2-propenyloxy                                          13.41   Br     2-Pentenyloxy                                                   13.42   Br     3-Pentenyloxy                                                   13.43   Br     3-chloro-2-propenyloxy                                          13.44   Br     2,3-Dichloro-2-propenyloxy                                      13.45   Br     2,3,3-Tri-chloro-propenyloxy                                    13.46   Br     2-propynyloxy                                                   13.47   Br     2-butynyl-oxy                                                   13.48   Br     3-butynyl-oxy                                                   13.49   Br     1-Methyl-2-propynyloxy                                          13.50   Br     Cyclopropyl                                                     13.51   Br     Cyclobutyl                                                      13.52   Br     Cyclopentyl                                                     13.53   Br     Cyclohexyl                                                      13.54   Br     2-Cyclopentenyl                                                 13.55   Br     1-Cyclopentenyl                                                 13.56   Br     2-Cyclohexenyl                                                  13.57   Br     1-Cyclohexenyl                                                  13.58   Br     Cyclopentyloxy                                                  13.59   Br     Cyclohexyloxy                                                   13.60   Br     2-Cyclopentenyloxy                                              13.61   Br     2-Cyclohexenyloxy                                               ______________________________________                                    

                  TABLE 14                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.1                                   ##STR27##                                                                                                      Phys. data                                    No.     R.sup.1                                                                               R.sup.7           mp [°C.]                               ______________________________________                                         14.1    I      i-C.sub.3 H.sub.7                                               14.2    I      n-C.sub.3 H.sub.7                                               14.3    I      n-C.sub.3 H.sub.7                                               14.4    I      sec.-C.sub.4 H.sub.9                                                                             97-98                                         14.5    I      i-C.sub.4 H.sub.9 148-149                                       14.6    I      tert.-C.sub.4 H.sub.9                                           14.7    I      n-C.sub.5 H.sub.11                                              14.8    I      sec.-C.sub.5 H.sub.11                                           14.9    I      n-C.sub.6 H.sub.12                                              14.10   I      n-C.sub.7 H.sub.15                                              14.11   I      sec.-C.sub.7 H.sub.15                                           14.12   I      1-Methylvinyl                                                   14.13   I      2-Methylvinyl                                                   14.14   I      Allyl                                                           14.15   I      2-Methylallyl                                                   14.16   I      2-Ethylallyl                                                    14.17   I      1-Methylallyl                                                   14.18   I      1-Ethylallyl                                                    14.19   I      1-Methyl-2-butenyl                                              14.20   I      l-Ethyl-2-butenyl                                               14.21   I      1-Isopropyl-2-butenyl                                           14.22   I      1-n-Butyl-2-butenyl                                             14.23   I      1-Methyl-2-pentenyl                                             14.24   I      1,4-Dimethyl-2-pentenyl                                         14.25   I      Propargyl                                                       14.26   I      2-butynyl                                                       14.27   I      3-butynyl                                                       14.28   I      Ethoxy                                                          14.29   I      Propoxy                                                         14.30   I      1-Methylethoxy                                                  14.31   I      n-Butoxy                                                        14.31   I      1-Methylpropoxy                                                 14.33   I      2-Methylpropoxy                                                 14.34   I      1,1-Dimethylethoxy                                              14.35   I      n-Pentyloxy                                                     14.36   I      n-Hexyloxy                                                      14.37   I      2-Ethylhexyloxy                                                 14.38   I      2-Propenyloxy                                                   14.39   I      2-Butentyloxy                                                   14.40   I      2-Methyl-2-propenyloxy                                          14.41   I      2-Pentenyloxy                                                   14.42   I      3-Pentenyloxy                                                   14.43   I      3-chloro-2-propenyloxy                                          14.44   I      2,3-Dichloro-2-propenyloxy                                      14.45   I      2,3,3-Trichloro.-propenyloxy                                    14.46   I      2-propynyloxy                                                   14.47   I      2-butynyl-oxy                                                   14.48   I      3-butynyl-oxy                                                   14.49   I      1-Methyl-2-propynyloxy                                          14.50   I      Cyclopropyl                                                     14.51   I      Cyclobutyl                                                      14.52   I      Cyclopentyl                                                     14.53   I      Cyclohexyl                                                      14.54   I      2-Cyclopentenyl                                                 14.55   I      1-Cyclopentenyl                                                 14.56   I      2-Cyclohexenyl                                                  14.57   I      1-Cyclohexenyl                                                  14.58   I      Cyclopentyloxy                                                  14.59   I      Cyclohexyloxy                                                   14.60   I      2-Cyclopentenyloxy                                              14.61   I      2-Cyclohexenyloxy                                               ______________________________________                                    

                  TABLE 15                                                         ______________________________________                                         Compounds of the formula V where A is A.sub.3                                   ##STR28##                                                                                                Phys. data                                          No.      R.sup.7           mp [°C.]                                     ______________________________________                                         15.1     i-C.sub.3 H.sub.7                                                     15.2     n-C.sub.3 H.sub.7                                                     15.3     n-C.sub.4 H.sub.9                                                     15.4     sec.-C.sub.4 H.sub.9                                                                             78-80                                               15.5     i-C.sub.4 H.sub.9 106-107                                             15.6     tert.-C.sub.4 H.sub.9                                                 15.7     n-C.sub.5 H.sub.11                                                    15.8     sec.-C.sub.5 H.sub.11                                                 15.9     n-C.sub.6 H.sub.13                                                    15.10    n-C.sub.7 H.sub.15                                                    15.11    sec.-C.sub.7 H.sub.15                                                 15.12    Ethoxy                                                                15.13    Propoxy                                                               15.14    1-Methylethoxy                                                        15.15    n-Butoxy                                                              15.16    1-Methylpropoxy                                                       15.17    2-Methylpropoxy                                                       15.18    1,1-Dimethylethoxy                                                    15.19    n-Pentyloxy                                                           15.20    n-Hexyloxy                                                            15.21    cyclopentyl                                                           15.22    Cyclohexyl                                                            15.23    2-Cyclopentenyl                                                       15.24    1-Cyclopentenyl                                                       15.25    2-Cyclohexenyl                                                        15.26    1-Cyclohexenyl                                                        15.27    Cyclopentyloxy                                                        15.28    Ethoxy                                                                15.29    Propoxy                                                               15.30    1-Methylethoxy                                                        15.31    n-Butoxy                                                              15.32    1-Methylpropoxy                                                       15.33    2-Methylpropoxy                                                       15.34    1,1-Dimethylethoxy                                                    15.35    n-Pentyloxy                                                           15.36    n-Hexyloxy                                                            15.37    2-Ethylhexyloxy                                                       15.38    2-Propenyloxy                                                         15.39    2-Butentyloxy                                                         15.40    2-Methyl-2-propenyloxy                                                                           oil                                                 15.41    2-Pentenyloxy                                                         15.42    3-Pentenyloxy                                                         15.43    3-chloro-2-propenyloxy                                                15.44    2,3-Dichloro-2-propenyloxy                                            15.45    2,3,3-Trichloropropenyloxy                                            15.46    2-Propynyloxy                                                         15.47    2-Butynyl-oxy                                                         15.48    3-Butynyl-oxy                                                         15.49    1-Methyl-2-propynyloxy                                                15.50    Cyclopropyl                                                           15.51    Cyclobutyl                                                            15.52    Cyclopentyl                                                           15.53    Cyclohexyl                                                            15.54    2-Cyclopentenyl                                                       15.55    1-Cyclopencenyl                                                       15.56    2-Cyclohexenyl                                                        15.57    1-Cyclohexenyl                                                        15.58    Cyclopentyloxy    oil                                                 15.59    Cyclohexyloxy                                                         15.60    2-Cyclopentenyloxy                                                    15.61    2-Cyclohexenyloxy oil                                                 15.62    1-Ethylpropoxy    oil                                                 ______________________________________                                    

The invention further relates to the following novel compounds.

Nicotinic anilide derivatives of the general formula I ##STR29## where the substituents have the following meanings: R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl,

R² unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -c₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆ -cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆ -cycloalkenyloxy, with the proviso that R² is not isopropyl when R¹ is chlorine.

Anilide derivatives of the general formula II ##STR30## where the substituents have the following meanings: ##STR31## X methylene or sulfur R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenloxy

with the proviso that

A is not A₁ when R is ethoxy, isopropoxy or allyloxy,

A is not A₂, X denoting sulfur, when R is ethoxy, propoxy, n-butoxy, sec.-butoxy or n-pentyloxy,

A is not A₂, X denoting methylene, when R is isopropyl.

2-Aminobiphenyl derivatives of the general formula III, ##STR32## where the substituents have the following meanings: ##STR33## X methylene, sulfur, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen.

Carboxanilide derivatives of the general formula V ##STR34## where the substituents have the following meanings: ##STR35## n 1 or 2 R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine

R⁵ methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy, with the proviso that R⁷ is not 3-methylbut-2-en-1-yl or 3-methyl- but-3-en-1-yl when R¹ is trifluoromethyl.

The novel compounds are suitable as fungicides.

The fungicidal compounds according to the invention, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.

Normally, the plants are sprayed or dusted with the active ingredients, or the seeds of the plants are treated with the active ingredients.

The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin-sulfite waste liquors and methylcellulose.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 1.7 and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 1.8, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 1.3, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.

IV. An aqueous dispersion of 20 parts by weight of compound no. 1.4, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.

V. A hammer-milled mixture of 80 parts by weight of compound no. 1.5, 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 1.7 and 97 parts by weight of particulate kaolin. The dust contains 3wt % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 1.8, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 1.9, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 1.33, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

The novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular Botrytis. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The compounds are applied by treating the fungi or the seeds, plants or materials threatened by fungus attack, or the soil with a fungicidally effective amount of the active ingredients.

The agents may be applied before or after infection of the materials, plants or seeds by the fungi.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Fusarium and Verticillium species in various plants,

Alternaria species in fruit and vegetables.

Use against Botrytis is preferred.

The novel compounds may also be used for protecting materials (timber), e.g., against Paecilomyces variotii.

The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient.

The application rates depend on the type of effect desired, and range from 0.02 to 3 kg of active ingredient per hectare.

When the active ingredients are used for treating seed, rates of 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally sufficient.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and other fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions.

Examples of fungicides which may be combined with the novel compounds are:

sulfur,

dithiocarbamates and their derivatives, such as

ferric dimethyldithiocarbamate,

zinc dimethyldithiocarbamate,

zinc ethylenebisdithiocarbamate,

manganese ethylenebisdithiocarbamate,

manganese zinc ethylenediaminebisdithiocarbamate,

tetramethylthiuram disulfides,

ammonia complex of zinc N,N'-ethylenebisdithiocarbamate,

ammonia complex of zinc N,N'-propylenebisdithiocarbamate,

zinc N,N'-propylenebisdithiocarbamate and

N,N'-polypropylenebis(thiocarbamyl) disulfide;

nitro derivatives, such as

dinitro(1-methylheptyl)-phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,

2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and

diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as

2-heptadecylimidazol-2-yl acetate,

2,4-dichloro-6-(o-chloroanilino)-s-triazine,

O,O-diethyl phthalimidophosphonothioate,

5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,

2,3-dicyano-1,4-dithioanthraquinone,

2-thio-1,3-dithio[4,5-b]quinoxaline,

methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,

2-methoxycarbonylaminobenzimidazole,

2-(fur-2-yl)-benzimidazole,

2-(thiazol-4-yl)benzimidazole,

N-(1,1,2,2-tetrachloroethylthio) -tetrahydropththalimide,

N-trichloromethylthiotetrahydrophthalimide,

N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N', N'-dimethyl-N-phenylsulfuric acid diamide,

5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

2-thiocyanatomethylthiobenzothiazole,

1,4-dichloro-2,5-dimethoxybenzene,

4-(2-chlorophenylhydrazono)-3-methyl -5-isoxazolone,

2-thiopyridine 1-oxide,

8-hydroxyquinoline and its copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide,

2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,

2-methylfuran-3-carboxanilide,

2,5-dimethylfuran-3-carboxanilide,

2,4,5-trimethylfuran-3-carboxanilide,

2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,

N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide,

2-methylbenzanilide,

2-iodobenzanilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal,

piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl) -formamide),

1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine and its salts,

2,6-dimethyl-N-cyclododecylmorpholine and its salts,

N [3-(p-tert.-butylphenyl) -2-methylpropyl]-cis-2,6-dimethylmorpholine

N-3-(p-tert.-butylphenyl) -2-methylpropyl'-piperidine,

1-2-(2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl'-1H-1,2,4-triazole,

1-[2-(2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-tri-azol-1-yl)-butan-2-one,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol,

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,

5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine,

bis -(p-chlorophenyl)-3-pyridinemethanol,

1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene,

1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

and various fungicides, such as

dodecylguanidine acetate,

3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide,

hexachlorobenzene,

DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,

methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,

N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone,

methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,

5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,

3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,

3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,

2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide,

1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,

2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol,

N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, and

1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

USE EXAMPLES

The active ingredients 2-chloronicotic acid-2'-ethylanilide (A)--disclosed in U.S. Pat. No. 4,001,416--and 2-chloronicotic acid-3'-isopropylanilide (B)--disclosed in DE 26 11 601 --were used for comparison purposes.

USE EXAMPLE 1

Action on Botrytis cinerea in paprika

Slices of green paprika pods were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. Two hours after the sprayed-on layer had dried, the slices were inoculated with a spore suspension of the fungus Botrytis cinerea, which contained 1.7×10⁶ spores per ml of a 2% strength malt solution. The inoculated slices were then incubated in humid chambers at 18° C. for 4 days. The development of Botrytis on the slices attacked was then assessed visually.

The results show that active ingredients 1.5, 1.7 and 1.8, applied as spray liquors containing 500 ppm of active ingredient, have a better fungicidal action (95%) than prior art comparative compounds A (10%) and B (65%).

USE EXAMPLE 2

Action on Botrytis cinerea in paprika

Paprika pods were slit open and the inside surfaces were sprayed to runoff with aqueous active ingredient formulations containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the pieces were inoculated with an aqueous suspension containing 1.7×10⁶ spores of Botrytis cinerea per ml.

The paprika pieces were then kept for 4 days in climatic cabinets at 20°-22° C. The extent of fungus spread was then assessed visually.

The results show that compounds 2.4, 4.4, 6.4, 7.4, 7.5, 9.1, 9.2, 9.4, 9.5, 10.1, 10.2, 10.4, 10.5, 12.4, 12.6, 2.65 and 2.66, applied as aqueous spray liquors containing 1,000 ppm of active ingredient, have a good fungicidal action (100%). 

We claim:
 1. A method for treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a compound of formula ##STR36## wherein A has the following meaning: thiazol-5-yl substituted in the 2- and 4-positions by hydrogen, methyl, chlorine or trifluoromethyl; andR has the following meanings: unsubstituted C₃ -C₁₂ -alkyl, unsubstituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkenyloxy, or phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₃ -C₄ alkylthio or halogen;in a suitable carrier.
 2. A method for treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a 2-aminobiphenyl compound of formula III ##STR37## wherein A has the following meaning: ##STR38## R⁴ methyl, trifluoromethyl, or chlorine; R⁵ is hydrogen, methyl, or chlorine; andR⁸ is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen; in a suitable carrier.
 3. A method for treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a 2-aminobiphenyl compound of formula IV ##STR39## wherein A has the following meaning: ##STR40## wherein R⁴ and R⁵ are as follows: R⁴ is methyl and R⁵ is hydrogen; or R⁴ is methyl and R⁵ is chlorine; or R⁴ is trifluoromethyl and R⁵ is hydrogen; or R.sup. 4 is trifluoromethyl and R⁵ is methyl; or R.sup. 4 is trifluoromethyl and R⁵ is chlorine; or R⁴ is chlorine and R⁵ is hydrogen; or R⁴ is chlorine and R⁵ is methyl; or R⁴ is chlorine and R⁵ is chlorine;in a suitable carrier.
 4. A method for treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a carboxanilide compound of formula V ##STR41## wherein A has the following meaning: ##STR42## R³ is methyl, trifluoromethyl, or chlorine; R⁴ is hydrogen, methyl, or chlorine; andR⁷ is unsubstituted C₃ -C₁₂ -alkyl, unsubstituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C.sub. 6-cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkenyloxy,in a suitable carrier.
 5. Aminobiphenyl compounds of formula III ##STR43## wherein A has the following meaning: ##STR44## R.sup. 4 is methyl, trifluoromethyl, or chlorine; R⁵ is hydrogen, methyl, or chlorine; andR⁸ is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen.
 6. Aminobiphenyl compounds of formula IV ##STR45## wherein A has the following meaning: ##STR46## wherein R⁴ and R⁵ are as follows: R⁴ is methyl and R⁵ is hydrogen; or R⁴ is methyl and R⁵ is chlorine; or R⁴ is trifluoromethyl and R⁵ is hydrogen; or R.sup. 4 is trifluoromethyl and R⁵ is methyl; or R⁴ is trifluoromethyl and R⁵ is chlorine; or R⁴ is chlorine and R⁵ is hydrogen; or R⁴ is chlorine and R⁵ is methyl; or R⁴ is chlorine and R⁵ is chlorine.
 7. Carboxanilide compounds of formula V ##STR47## wherein A has the following meaning: ##STR48## R³ is methyl, trifluoromethyl, or chlorine; R⁴ is hydrogen, methyl, or chlorine; andR⁷ is unsubstituted C₃ -C₁₂ -alkyl, unsubstituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy, with the proviso that R⁷ is not 3-methyl-but-2-en-1-yl or 3-methyl-but-3-en-1-yl when R¹ is trifluoromethyl.
 8. A composition for treating Botrytis infestation comprising an effective amount of a compound of formula ##STR49## wherein A has the following meaning: thiazol-5-yl substituted in the 2- and 4-positions by hydrogen, methyl, chlorine or trifluoromethyl; andR has the following meanings: unsubstituted C₃ -C₁₂ -alkyl, unsubstituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkenyloxy, or phenyl which is substituted by C₁ -C₄ -alkyl, C₄ -C₆ -alkoxy, C₁ -C₄ -alkylthio or halogen;in a suitable carrier.
 9. A composition for treating Botrytis infestation comprising an effective amount of a 2-aminobiphenyl compound of claim 5 in a suitable carrier.
 10. A composition for treating Botrytis infestation comprising an effective amount of a 2-aminobiphenyl compound of claim 6 in a suitable carrier.
 11. A composition for treating Botrytis infestation comprising an effective amount of a carboxanilide compound of claim 7 in a suitable carrier. 